10 Writing Rules You Can (and Should) Break

By Max Winter
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Jul 14, 2017

The immersive and accomplished debut novel by Max Winter,Exes, is haunted as much by the city of Providence, R.I., as it is by the suicide of Eli, brother of Clay Blackall, one of several narrators in this novel in fragments who each provide insight into why Eli might have ended his life. A writer of remarkable empathy, complexity, and humor, Winter shares 10 old and tired writing "rules" that you should break.

Let me begin by reminding you—and myself, because of certain things we must routinely remind ourselves, too—that there are, in fact, no rules in fiction. Like, none. (Hell, in this context, the word rule should probably even appear in quotes, just as, say, “reality” has since—when?—1920? 1945? ’53? From November 8, 2016 on, for sure.) And also by reminding us that this general rulelessness is almost certainly a big part of what made us want to write the stuff in the first place. (Remember that joyful whoop that would surge through the classroom whenever Teacher announced that the next assignment was to be creative? Exactly.) Why, if we wanted to follow rules we would’ve leapt to become the low-to-mid-level employees that we’ve had to be anyway in order to buy ourselves all the time we need to learn how to not follow any goddamned rules for a change. Because, regardless of what all these rule enforcers like to tell themselves and others, breaking rules really means writing new ones of your own, which, of course, is way harder than simply following the ones other people came up with. But regardless of how you feel about rules, so long as you’re willing to break them now and then, here are 10 that you should absolutely have at:

1. Show don't tell

The go-to comment of the beleaguered high school English teacher (and I say this is as a former beleaguered high school English teacher—one who wasn’t above scrawling this exact phrase in margins of especially vague personal essays about things like rollercoasters and grandmothers). Like the proverbial and actual stopped clock, it’s right twice a day. Okay, it’s right a lot more than that, but still… Does Henry James mind telling you things now and then? How about Toni Morrison? Tolstoy? Point being, sometimes it’s simply more efficient and, indeed, more interesting—especially if the point itself is nuanced and complex and multivalent—just to come out and say it: “‘She would of been a good woman,’ the Misfit said, ‘if it had been someone there to shoot her every minute of her life.’” Or, “I am an invisible man,” a short, direct statement so endlessly complex that it takes every last one of the book’s nearly 600 pages to get us to the point where we “almost have it.” Or, hell, how about, “To be, or not be?” Point being, as often as not—and not for nothing—these are the lines that eventually become quotes.

2. Your main character must be "likable"

To be fair, this one may be more of a “market demand” than an actual “rule,” but still: bullshit. Characters needn’t be “likable,” whatever the hell that means—and, rest assured, it means wildly different things to different people—they only need be “interesting,” to borrow Henry James’ preferred term. Is Richard III likable? Yunior de Las Casas? Hulga Hopewell? Father Urrutia? Humbert Humbert? Do they need to be? Okay, why? Sorry, but for this one, I’m afraid the burden of proof lies with this rule’s adherents. Let’s see a single person defend it in a way that makes them sound like neither a focus group participant nor someone who just wants to pretend-hang out with imaginary word-people in a book-shaped clubhouse. Have fun, you two!

3. Write what you know

Another old saw based in some truth—this time having to do with not, you know, talking out of your ass and/or misrepresenting someone else’s experience, neither of which, for reasons having nothing to do with literature, are particularly good ideas—but that has, over time, and in the aggregate, maybe done more harm than good, in that it is the kind of advice that closes doors rather than opens them. Here, again, it helps to remember why we got into this whole farkakte fiction-writing “business” to begin with: because we wanted to see what was behind that door, if not to break it down altogether. Because writers are born snoops and eavesdroppers and gossips and sneaky little diary readers just about driven by what we don’t know. We’re not expressing ourselves in our writing so much as we are searching for the otherwise inexpressible. No, a better “rule”—which will end up covering the original’s intent, but not at the expense of new experiences—is simply to write what interests you, healthily or otherwise. Are we interested in what we know? Perhaps. Do we write to better understand what we do not know? Oh, absolutely. Because what we don’t know could fill a book.

4. Avoid pop-cultural references

Fittingly, this one all but begs to be responded to by way of that Gene-Wilder-as-Willie-Wonka meme. So, you’re concerned not with the already-unlikely-enough odds against your work ever being read now, but with the almost literally astronomical odds of your work being read in the future? Tell me more. Yeah, no, that’s not pretentious at all… I’d say let me know how this turns out for you, but we’ll both be dead.

But anyway, in the meantime, go ahead and use a Full House reference and take comfort in knowing that that is not what’s dooming your work to what will almost certainly become total obscurity. Besides, if your literal-once-in-a-generation work does, in fact, turn out to be deathless enough to survive time’s myriad upheavals, future academics will, you know, like, add footnotes and stuff. You’ll be fueling the You industry!

5. Don't digress

You know what book has a lot of digressions in it? Moby-Dick. Same with Tristram Shandy, Gravity’s Rainbow, White Noise. Nicholson Baker’s still-fresh The Mezzanine is just about made out of digressions, or—as Baker calls them in his every bit as great U and I—“narrative clogs.” Meanwhile, even people who haven’t read David Foster Wallace’s work know that its digressions have digressions in them. That these books aren’t for everyone is the whole point. Because so many of these so-called rules are simply matters of taste reverse-engineered into plausible-sounding imperatives, which is exactly as gross as it sounds and reason enough to break them.

6. Don't leave a character alone

…On the page… For any length of time. What, you mean like how Leopold Bloom is by himself for, like, a third of the book? Or how Mrs. Ramsay is? Or Nick Adams? Or Ivan Ilyich? How about Hamlet, again? Besides which, a character is never alone on a page, because there’s always an author to keep him company. And then a reader…

7. Don't write about music

Or, as someone once (admittedly) brilliantly put it, “Writing about music is like dancing about architecture.” Well, two of my—and countless other readers’—favorite passages in all of 20th Century literature are Ralph Ellison and James Baldwin describing Louis Armstrong’s trumpet and Sonny’s piano, respectively. Both passages are as moving—and as, well, musical—as any pieces of actual music ever played. Plus, if the various modes of artistic expression are hand shapes thrown in a game of rock-paper-scissors, then fiction is some loudmouthed bully of an older brother’s invented fourth shape. Then he dead-arms everyone for good measure. So have at it! (Plus, even if it is like dancing about architecture, who wouldn’t want to see that?)

8. Avoid jokes

Anyone who’s read my book, Exes, already knows where I stand on this one, which may very well be more of a critical expectation of “serious fiction” (whatever that is) than a rule, per se, but that doesn’t mean it isn’t total crapola. Don’t take it from me, though. Take it from Laurence Sterne, and from Cervantes, and Nabokov, and George Saunders, and Rebecca Schiff, and Gary Shteyngart, and Aimee Bender, and Wells Tower, and Courtney Maum, and Matt Sumell, and…

For those who may say, well, sure, but being funny limits your audience and/or anchors it to a certain time/place/set of cultural expectations, see item #4 on this list; and also, this is not necessarily, you know, true. Why, just the other night, I laughed out loud—repeatedly—while reading—in translation, mind you—Machado de Assis’s still-funny-after-118-years novella The Alienist. Plus, you know what else ages poorly? Plot, character, theme, dialogue, in other words, pretty much everything except for Blazing Saddles, single-malt Scotch, and Angela Bassett. Oh, and A Midsummer’s Night Dream’s never-not-funny play-within-a-play.

9. Less is more

I mean, okay, sometimes—if not mostly—it is, but that’s the whole problem with rules, isn’t it? That unspoken “always”? "Always" is a bullshit word. Fuck "always." And not everyone needs to be Hemingway or Carver or even Lydia Davis. As Proust, Eliot, and our good friend Henry James—among many, many others—prove, more can be more, too. Just as less can also be less. (“Such terrible writing!” We say, closing the book. “I know,” we think, hefting it, “and such small portions!”)

10. The fallacy of imitative form

Even if you don’t immediately recognize Yvor Winters’s term, you’ve almost certainly received this advice in some workshop, in some form or another, and, in all likelihood, from that guy.* It’s predicated on the suspect notion that you cannot recreate the shape of that which you’re describing on a sentence level without somehow alienating or confusing the reader, to which I respond, hogwash, and present as my evidence maybe my favorite consecutive three lines from maybe my favorite book: the late, great Denis Johnson’s Jesus' Son:

“Or maybe that wasn’t the time it snowed. Maybe it was the time we slept in the truck and I rolled over on the bunnies and flattened them. It doesn’t matter.”

Or, from the same book, some 60 pages after the book’s narrator, Fuckhead, told us a story about one man, rather than the two he had promised:

“But I never finished telling you about the two men.”

Or from any sentence in the entire book, really, because it’s just about made out of the imitative form, because Fuckhead can’t keep anything straight; and it proves with every perfect sentence that, in the right hands, such an approach is not only not a fallacy, but, in fact, a verity. Or, as Fuckhead himself puts it, when describing yet another man:

“Will you believe me when I tell you there was kindness in his heart? His left hand didn't know what his right hand was doing. It was only that certain important connections had been burned through. If I opened up your head and ran a hot soldering iron around in your brain, I might turn you into someone like that.”

In other words, there but for the grace of god, go I. And go you. But to fully realize this, you first need to walk a highway mile in Fuckhead’s shoes, tattered and filled with raindrops, every one of which has its own name… It’s always worth remembering that fiction is, above all else, an exercise in empathy. “And you, you ridiculous people,” he says, early on, “you expect me to help you.”

It’s maybe my favorite book—one which breaks a lot of rules (nearly all of them, in fact) and is as funny as hell, to boot. And isn’t that the whole point? Why follow a bunch of made-up rules that will only make your work less like what you love? Just figure out what interests you, try your best to get there, then once you do, write some directions so other people can join you if they’re interested.

*Full disclosure: For a while there, I’m pretty sure I was that guy. Then I read Jesus’ Son…

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